Dimethylformamide → 1-hydroxy-3-(oxiran-2-ylmethoxy)-12H-benzo[b]xanthen-12-one

HRID 83109

反応式

HRID 83109 の反応式
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[CH:12]=[C:11]4[CH:17]=[CH:18][CH:19]=[CH:20][C:10]4=[CH:9][C:8]=3[O:7][C:6]=2[CH:5]=[C:4]([OH:21])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C.[CH2:33]([CH:35]1[O:37][CH2:36]1)Cl>O>[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[CH:12]=[C:11]4[CH:17]=[CH:18][CH:19]=[CH:20][C:10]4=[CH:9][C:8]=3[O:7][C:6]=2[CH:5]=[C:4]([O:21][CH2:33][CH:35]2[CH2:36][O:37]2)[CH:3]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 107077051,3-dihydroxy-12H-benzo(b)xanthen-12-one

生成物 1

HCID 462326461-hydroxy-3-(oxiran-2-ylmethoxy)-12H-benzo[b]xanthen-12-one収率 10.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

1,3-dihydroxy-12H-benzo[b]xanthen-12-one (0.1 g, 0.36 mmol) synthesized in Step 1 of Example 18, K2CO3 (0.2 g, 1.44 mmol), and DMF (5 mL) were added to a dry round-bottom flask, and epichlorohydrin (0.19 g, 2.16 mmol) was added thereto with stirring using a syringe. The reaction mixture was stirred under a nitrogen atmosphere (75° C., overnight). After the reaction was completed, water was added to the reaction mixture which was then extracted twice with ethyl acetate. The organic layer was combined, washed with brine and dried over anhydrous Na2SO4. This liquid was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was separated and purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:3 (v/v)) to give the title compound (13 mg, 10.8%) as a yellow solid.

後処理

  1. stirringThe reaction mixture was stirred under a nitrogen atmosphere (75° C., overnight)
  2. extractionwas then extracted twice with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationThis liquid was filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was separated
  8. custompurified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:3 (v/v))

出典と根拠

ORDレコード
ord-5b10a7674ef2473ab6300333901e8b9f
出典データセット
uspto-grants-2014_09
特許番号
US08846749B2

関連ノート

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